CuH-catalyzed asymmetric 1,4-reduction of α, β-unsaturated amides

CHED 372

Bruce H. Lipshutz, lipshutz@chem.ucsb.edu, Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, Jeff M. Servesko, Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106, David B. Ball, dball@csuchico.edu, Department of Chemistry, California State University, Chico, Chico, CA 95929-0210, and Jennifer H. Howell, dball@csuchico.edu, Chemistry Department, California State University, Chico, CA 95929-0210.
Asymmetric induction β to carbonyl functionalities offers access to a wealth of structural arrays that can be utilized in synthetic strategies of complex molecules. Chelation by modern bidentate phosphine ligands induces an extreme stereochemical bias in CuH reactions. Takasago's SEGPHOS family of nonracemic bis-phosphine ligands when complexed with CuH have been shown to exert remarkably high degrees of facial selectivity in 1,4-reductions of α, β -unsaturated enones. Methodology based on a specific non-racemic ligand L* [(R)-(-)-DTMB- SEGPHOS] that chelates Cu (I), presumably was CuH, leading to asymmetric 1,4-reduction of α, β-unsaturated amides will be presented.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Chemical Education

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006